Acetic Acid → Ethyl 3-(5-(2-(((2-chloro-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)amino)methyl)-3-methyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

HRID 405253노트

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HRID 405253 반응식
[CH:1]([C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]([F:13])([F:12])[F:11])=[CH:5][C:4]=1[C:14]1[CH:15]=[CH:16][C:17]([C:20]([NH:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:21])=[N:18][CH:19]=1)=O.[Cl:30][C:31]1[CH:36]=[C:35]([NH2:37])[CH:34]=[CH:33][C:32]=1[C:38]1[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][CH:39]=1.CC(O)=O.[BH3-]C#N.[Na+].[NH4+].[Cl-]>CCO>[Cl:30][C:31]1[CH:36]=[C:35]([NH:37][CH2:1][C:3]2[C:8]([CH3:9])=[CH:7][C:6]([C:10]([F:12])([F:13])[F:11])=[CH:5][C:4]=2[C:14]2[CH:15]=[CH:16][C:17]([C:20]([NH:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:21])=[N:18][CH:19]=2)[CH:34]=[CH:33][C:32]=1[C:38]1[CH:43]=[CH:42][C:41]([C:44]([F:45])([F:46])[F:47])=[CH:40][CH:39]=1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 5003444Sodium cyanoborohydrideHCID 688342842-Chloro-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-amineHCID 86674283Ethyl 3-(5-(2-formyl-3-methyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

생성물 1

HCID 86674284Ethyl 3-(5-(2-(((2-chloro-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)amino)methyl)-3-methyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
80 °C

실험 절차

Ethyl 3-(5-(2-formyl-3-methyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate (37 mg, 0.09 mmol), 2-chloro-4′-(trifluoromethyl)-[1,1-biphenyl]-4-amine (39 mg, 0.14 mmol) and HOAc (5 μL, 0.09 mmol) were dissolved in EtOH (2 mL) and the resulting mixture was heated to 80° C. After 5 h the resulting mixture was cooled to room temperature, solid NaCNBH3 (28 mg, 0.45 mmol) was added and the resulting mixture was stirred at room temperature. After 2 h saturated aqueous NH4Cl was added and the aqueous phase was extracted with EtOAc. The combined organics were dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

후처리

  1. temperatureAfter 5 h the resulting mixture was cooled to room temperature
  2. extractionthe aqueous phase was extracted with EtOAc
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified via column chromatography

출처 및 근거

ORD 기록
ord-28a5570787624e5a932a57911170a02c
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748624B2

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